Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 31, Pages 9047-9051Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503297
Keywords
cross-coupling; fluorine; homogeneous catalysis; nickel; zinc
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Funding
- National Institutes of Health (National Institute of General Medical Sciences) [R01-GM62871]
- Gordon and Betty Moore Foundation (Caltech Center for Catalysis and Chemical Synthesis)
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Fluorinated organic molecules are of interest in fields ranging from medicinal chemistry to polymer science. Described herein is a mild, convenient, and versatile method for the synthesis of compounds bearing a perfluoroalkyl group attached to a tertiary carbon atom by using an alkyl-alkyl cross-coupling. A nickel catalyst derived from NiCl(2)glyme and a pybox ligand achieves the coupling of a wide range of fluorinated alkyl halides with alkylzinc reagents at room temperature. A broad array of functional groups is compatible with the reaction conditions, and highly selective couplings can be achieved on the basis of differing levels of fluorination. A mechanistic investigation has established that the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) inhibits cross-coupling under these conditions and that a TEMPO-electrophile adduct can be isolated.
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